Dihydroaromatic cyanamides



Patented Mar. 19, 1940 v onrrso sTA-jrss PATENT" orrice 2,194,075 DIIHYDROAROMATIC GYANAMIDKES Richard Roblim Jr., Stamford, Coma, assignor to American Cyanamid Company, New York,

Y., acorporation of Maine No Drawing. Application May 23, 1939,

Serial No. 275,217

4 Claims.

'15 follows:

NIELHCl Example I 6.1 grams of cyanogen chloride are dissolved in 200 cc. of benzene. After cooling the solution tow- C., gradually added with stirring. When this addition is. completed, the dicyclohexyl aminehydrochloride is filtered off and Washed with benzene. The washings and. filtrate are united. The benzene is removed by distillation under reduced 30 pressure. The residue is vacuum distilled'and the product identified dicyclohexyl cyanamide.

Example II 6.1 grams of cyanogen chlorideare dissolved in 200 cc. of h'epta'ne. After cooling the solution to 0-5 C., 41.8 grams of di-(Z-methyl cyclohexyl) amine are gradually added with stirring. When this addition is completed, the di(2-methyl cyclohexyl) amine hydrochloride is filtered off and 40 washed with heptane. Thewashings and filtrate are united. The heptane is removed by distilla- 't ion under reduced pressure. The residue is vacuum distilled and the product identified as di- (Znnethyl cyclohexyl) cyanamide.

' 5 Example 111 6.1 grams of cyanogen chloride. are dissolved in 200 cc. of benzene. After cooling the solution 5 tov 025 0., 41.8 grams of di-(3-methyl cyclohexyl) amine are gradually added with stirring. When this addition is completed, the (ii-(3- methyl cyclohexyl) amine hydrochloride is filtered off and washed with benzene. The washings 55 and filtrate are united. The benzene is removed 36.2 grams of dicyclohexyl amine are by distillation under reduced pressure. The residue is vacuum distilled and the product identified as di-(B- methyl cyclohexyl) cyanamide.

Example IV 6.1 grams of cyanogen chloride are dissolved in 200 cc. of heptane. After cooling the solution to'05 C., 41.8 grams of di-(e-methyl cyclohexyl) amine are gradually added with stirring. When this addition is completed, the dii-methyl cyclohexyl) amine hydrochloride is filtered off andwashed with heptane. The washings and filtrate are united. 'The heptane is removed by distillation under reduced pressure. The residue is vacuum distilled and theproduct identified as di-(4-methyl cyclohexyl) 'cyanamide.

Example V 6.1 grams of cyanogen chloride are dissolved in 200 ccm'of heptane. After cooling the solution to O-5 C., 47.4 grams of di-(2-ethyl cyclohexyl) amine are gradually added. with stirring. When this addition is completed, the di-(Z-ethyl cyclohexyl) amine hydrochloride, is filtered off and washed with heptane. The washings and filtrate are united. The heptane is removed by distillation under reduced pressure. 'The residue is vacl uum distilled and the product identified as di (2ethyl cyclohexyl) cyanamid'e.

. Example VI 6.1 grams of cyanogen chloride are dissolved in 250 cc. of benzene. After cooling the solution to 05 C., 64.2 grams of di-(n-amyl cyclo-hexyl) amine are gradually added with stirring. When this addition is completed, the di-(n-amyl cyclohexyl) amine hydrochloride is filtered ofi and washed with benzene. The washings and filtrate are united. The benzene is removed by distillation under reduced pressure. I The residue is vacuum distilled and the product identified as di- (n-amyl cyclohexyl) cyanamide.

Similarly other disubstituted cyanamides of the above class may be prepared utilizing the corresponding secondary amine.

It is to be understood that the above examples are illustrative only. i

These new compounds are adapted for various uses, more particularly as intermediates and insectieides.

While the invention has been described with 'particular'reference to specific embodiments, it is to be understood that it is not to be limited thereto but is to be construed broadly and restricted solely by the scope of the appended where R and R each represent a hydroaromatic claims. radical.

I claim: 2. As a new compound, dicyclohexyl cyanamide. 1. As a new compound, a disubstituted cyan- 3. As a new compound, di-(4-methylcyc1o- 5 amide of the formula hexyl) cyanamide.

R 4. As a, new compound, di-(Z-ethylcyclohexyl) cyanamide. RICHARD o. ROBLIN, JR. 

